This Week in Key West: July 27 - August 2, 2026

Looking for things to do in Key West this week? Discover live music, local events, art walks, happy hours, nightlife, and island happenings taking place July 27 – August 2, 2026.

🌟 This Week at a Glance

🐾 Sloppy Joe’s Hemingway^® Look-Alike Contest
🎣 Key West Marlin Tournament
🎟️ Summer Bingo Night
🧑‍🌾 Key West Farmers Market
🎵 Live Music Every Day

🌟 This Week’s Highlights

🌅 Glow Hours at Hugh’s View

Tuesdays every week • The Studios of Key West Rooftop

Take in panoramic sunset views while enjoying drinks, art, and one of Key West’s newest rooftop experiences above The Studios of Key West.

🎟️ Summer Bingo Night

Wednesday, July 29 • Key West Theater • Free Entry • 6 pm

A fun, free community favorite with prizes, drinks, and plenty of laughs. Doors open at 6:00 PM and bingo begins at 7:00 PM.

🤓Jackpot Trivia

Thursday, July 22 @ Key West EmPOURium — 6–7:30 PM
Bring your besties and your brain power for a fun-filled night of trivia with host, Bill Hoebee. Free to attend. Win prizes! Sponsored by Pilar Rum and Bombara Vodka.

🦞 Key West Lobster Mini Season

July 29–30, 2026

One of Key West’s biggest summer traditions returns as recreational divers take to the water for the annual Lobster Mini Season. Marinas buzz with activity, local restaurants serve up fresh seafood, and the island celebrates two days of unforgettable adventure on the water. Whether you’re hunting for spiny lobster or enjoying the lively waterfront atmosphere, it’s an exciting time to experience Key West.

👉 Learn more & get your license here: myfwc.com/fishing/saltwater/recreational/lobster/

🌴 Our Concierge Pick

⛵ Sunset Sail

Nightly • Key West Harbor

Watching the sunset from the water is one of the most memorable experiences in Key West. Whether you prefer a classic schooner, a spacious catamaran, or a lively cruise with live music and cocktails, there’s a sunset sail for every style.

💡 Concierge Tip: Sunset sails are one of our most popular recommendations and often sell out—especially on weekends. Reserve early for the best availability.

👉 Book Your Sunset Sail: Key West Sunset Sail Options

Planning a future trip to Key West?

Browse festivals, concerts, races, holiday celebrations, and special events happening throughout the year.

View our complete 2026 Key West Events Calendar →

🎵 Live Music & Entertainment

Monday, July 27

• Nick Norman @ Rams Head Southernmost — 11AM–2 PM
• Mary Spear @ The Gardens Hotel — 5–7 PM
• Colton Gleghorn @ Key West EmPOURium — 6–9 PM
• Charity Bingo @ Green Parrot Bar — 7–9 PM
• Martinis w/ Melodic Beats @ General Horseplay — 9 PM

Tuesday, July 28

• John Dion @ The Gardens Hotel — 5–7 PM
• Zack Seemiller @ Rams Head Southernmost — 6–9 PM
• Jesse James Russell @ Key West EmPOURium — 6–9 PM
• Actual Bank Robbers @ Sloppy Joe’s — 10 PM

Wednesday, July 29

• Sharese @ Rams Head Southernmost — 11 AM–2 PM
• Kenny Albert @ The Gardens Hotel — 5–7 PM
• A Pirate Looks Back: Jimmy Buffett Tribute Show @ Comedy Key West — 12:30 PM
• Line Dancing @ Key West EmPOURium — 6:30–8:30 PM
• Naked Karate Girls @ Sloppy Joe’s — 10 PM

Thursday, July 30

• Robert Douglas @ Rams Head Southernmost — 11 AM–2 PM
• Mac Calhoun @ Key West EmPOURium — 6–9 PM
• Chris Maloney @ Doc’s on Duval — 6–9 PM
• Elle Haley and the Why Nots @ General Horseplay— 9 PM
• Naked Karate Girls @ Sloppy Joe’s — 10 PM

Friday, July 31

• Andy Westcott @ Rams Head Southernmost — 11 AM–2 PM
• Happy Hour All Day @ The Roost — 12–6 PM
• The Fabulous Spectrelles @ the Karaoke Lounge-Key West EmPOURium — 7–8 PM
• Wichita Jack @ Doc’s on Duval — 6–9 PM
• Shastina @ General Horseplay — 7 PM
• ‘Unpspoke Bond’ Documentary Screening @ Key West Theater — 8 PM
• Naked Karate Girls @ Sloppy Joe’s — 10 PM

Saturday, August 1

• Aaron Blumer @ Rams Head Southernmost — 10:30 AM–1:30 PM
• Paul Warthen @ The Gardens Hotel — 5–7 PM
• Toko Irie @ The EmPOURium — 6–9 PM
• Jesse James Russell @ Doc’s on Duval — 6–9 PM
• Zach Lovering @ General Horseplay— 7 PM
• Naked Karate Girls@ Sloppy Joe’s — 10 PM

Sunday, August 2

• Marjorie Lee @ Rams Head Southernmost — 11 AM–2 PM
• Pierce August @ Mac’s Place —4:30 PM–7:30 PM
• Jazz in the Garden with John Dion @ The Gardens Hotel — 5–7 PM
• The Newtons @ Key West EmPOURium — 6–9 PM
• Naked Karate Girls @ Sloppy Joe’s — 10 PM